top of page

Accounting Department Cleanup
A practical series focused on restoring order to messy accounting departments. From policy breakdowns and procedural fixes to step-by-step cleanup strategies, each post helps founders and finance leaders rebuild structure, accuracy, and confidence in their financial reporting.


The Fragility of Cheap Accounting Solutions
When systems aren’t built to last, fragility eventually shows — just like these hollow trees. Every few years, headlines warn that automation is coming for our jobs. From factory floors to front offices, the fear is always the same: machines replacing humans. In accounting, the pitch sounds familiar, and it almost always arrives as a promise of efficiency. Artificial Intelligence (AI) is creeping into both ends of the spectrum—cheap bookkeeping tools and flashy dashboards for

Brett J. Federer, CPA
Sep 285 min read


Bookkeeper vs Controller: What Happens When Roles Blur
When boundaries blur, what looks solid quickly loses clarity — in nature and in accounting. Most founders don’t think much about accounting until the business reaches a point where it can’t be ignored. When that moment comes, titles like bookkeeper and controller often sound interchangeable — as if both simply mean “the person keeping the books.” It’s an understandable assumption, born from focusing on growth rather than finance. That assumption is also where the first cracks

Brett J. Federer, CPA
Sep 266 min read


Accounting Guardrails: When Structure Is Missing, Messiness Is Inevitable
When accounting lacks structure, it grows unruly — just like grass without trimming. The Hidden Source of Mess When a founder sees messy accounting, the first instinct is often to assume the people are the problem. Maybe the accountants aren’t as strong as expected. Maybe they’re not paying attention. Maybe they simply don’t care. But the truth is usually very different. In most cases, messy departments are made up of smart, capable accountants who are doing their best with w

Brett J. Federer, CPA
Sep 245 min read


The Hidden Cost of Reclassifying Transactions After the Close
Numbers can twist and turn, but a disciplined close keeps the path straight for leadership. You finish the month, your dashboards look good, and you send out the investor update. Two days later, someone notices a handful of transactions sitting in the wrong buckets — a big software invoice coded to Office Supplies, ads posted to COGS, or a contractor paid from the wrong class. The instinct says it’s no big deal because you can just reclass those after the close. Here’s the ha

Brett J. Federer, CPA
Sep 215 min read


Why Inconsistent Reconciliations Erode Trust
Like ice eroding in silence, unreconciled errors gradually weaken financial trust. In accounting, silence isn’t neutral — it compounds. A small error that slips through this month doesn’t vanish next month; it rides forward, embedding itself into every balance that follows. At first, the books still appear fine. Reports run, totals line up, and deadlines get met. But beneath the surface, those unchecked discrepancies accumulate. By the time they’re spotted, the cleanup is no

Brett J. Federer, CPA
Sep 164 min read


The Challenges of Leadership Undervaluing Accounting
When leadership undervalues accounting, standards erode like a building left untended — what once stood strong begins to crumble under neglect. Standards rarely collapse all at once — they fade as attention fades. When leadership undervalues accounting, the department slowly follows. At first, nothing looks broken: the numbers get reported, deadlines are met, and the surface appears stable. But without questions being asked or decisions relying on the data, the incentive to m

Brett J. Federer, CPA
Sep 154 min read


The Challenges of One-Person Accounting Departments (and Where to Start)
When one person carries the entire load, it’s only a matter of time before capacity runs out. One-person accounting departments don’t fail because of a lack of skill, but because the workload leaves no room for review, improvement, or rest. What seems lean and efficient in the early days often hides a growing strain that compounds month after month. At first, the deadlines are met, the reconciliations get done, and the books close on time — but beneath that surface, cracks be

Brett J. Federer, CPA
Sep 133 min read


Why Messy Accounting Departments Cost More Than You Think
Messy accounting is like navigating a tangled forest — hard to find your footing, and easy to lose direction. Messy accounting doesn’t usually appear as one big collapse. It creeps in slowly, one small breakdown at a time, until leaders realize they can’t fully trust the numbers in front of them. A variance here, a delayed report there, a lingering question from an investor — none of these on their own feel catastrophic, but together they form a pattern that undermines clarit

Brett J. Federer, CPA
Sep 136 min read


Navigating Tax Changes: The Importance of Clarity in Your Financial Systems
The One Big Beautiful Bill was signed on July 4, 2025 — a reminder that financial clarity matters when policy shifts. You don’t need to be a tax expert. You need a structure you can trust when things change. When a major tax law hits the headlines, most founders tend to fall into one of two camps. The first thinks, “That doesn’t apply to me.” The second shrugs and says, “I guess I’ll deal with it later.” Both reactions are understandable. You’re running a business, not studyi

Brett J. Federer, CPA
Aug 205 min read


Why AI + Bookkeeping Still Leaves Gaps — and Why Structure Still Matters
Like branches that guide growth, financial systems provide the support AI alone can’t. AI is changing how businesses handle their finances — fast. In the last few years, automation has moved from simply being “nice to have” to now being a default setting in the world of bookkeeping. Tools can now sync bank feeds, categorize transactions, reconcile accounts, and deliver reports with minimal human input. In many cases, this has led to real improvements: fewer errors, faster clo

Brett J. Federer, CPA
Aug 184 min read
bottom of page